1-Propanol → 2-Cyclopentyloxy-benzaldehyde

HRID 2227349Notes

Reaction equation

HRID 2227349 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:7](OC)=[C:5](O)[CH:4]=1.C[C:13]([CH3:16])([O-:15])[CH3:14].[K+].[CH2:18](O)[CH2:19]C>>[CH:13]1([O:15][C:4]2[CH:5]=[CH:7][CH:10]=[CH:11][C:3]=2[CH:2]=[O:1])[CH2:16][CH2:19][CH2:18][CH2:14]1

Participants

4

Reactant 3

HCID 10311-PropanolHCID 12127IsovanillinHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 31527232-Cyclopentyloxy-benzaldehydeYield 77.5%

Procedure

77.70 g (500 mmoles) of isovanillin and 69.40 g (600 mmoles) of 97% potassium t-butoxide (t-BuOK) dissolved in 800 ml of 1-propanol, 69.0 ml 630 mmoles), and the solution refluxed. After 3 hours another 9.25 g (80 mmoles) of t-BuOK were added at 80° C. and the suspension refluxed for another 3 hours. The solid was filtered off and the filtrate evaporated in vacuo to dryness. The residue was dissolved in ether and extracted with 1N NaOH. The ether phase was evaporated to dryness: 85.40 g (77.5%) of cyclopentyloxybenzaldehyde was isolated.

Workup

  1. temperature69.0 ml 630 mmoles), and the solution refluxed
  2. temperaturethe suspension refluxed for another 3 hours
  3. filtrationThe solid was filtered off
  4. customthe filtrate evaporated in vacuo to dryness
  5. dissolutionThe residue was dissolved in ether
  6. extractionextracted with 1N NaOH
  7. customThe ether phase was evaporated to dryness

Sources & evidence

ORD record
ord-4e3f3970edc94e6e9c8dc563cecca0a1
Source dataset
uspto-grants-2002_07
Patent number
US06413975B1

Reaction notes

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